The present invention relates to a new and distinct variety of strawberry (Fragaria×ananassa Duchesne) plant that is named ‘Winter Dawn’ and more particularly to a strawberry plant that is distinguished by its high fruit yield during the winter in west central Florida, as well as its ability to produce medium to large, easily harvestable fruit. Asexual propagation was performed at Dover, Fla. where the selection was made and plants were tested. Contrast is made to ‘Strawberry Festival’ (U.S. plant Pat. No. 14,739), currently the dominant variety in Hillsborough County, Fla., for reliable description. This new variety is a promising candidate for commercial success because it produces high fruit yields during a desirable market window. Also, because of its Colletotrichum crown rot resistance, it can be successfully propagated in Florida, giving Florida growers the option of propagating their own plants.